2-(2-Hydroxyphenyl)-4-thiazolecarboxylic acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00046 |
| CAS | 27501-91-3 |
| Molecular Weight | 221.23 |
| Molecular Formula | C10H7NO3S |
Online Inquiry
Description
2-(2-Hydroxyphenyl)-4-thiazolecarboxylic acid is a natural product found in Burkholderia cepacia.
Specification
| Synonyms | 2-(2-hydroxyphenyl)thiazole-4-carboxylic acid; Aeruginoic acid |
| IUPAC Name | 2-(2-hydroxyphenyl)-1,3-thiazole-4-carboxylic acid |
| Canonical SMILES | C1=CC=C(C(=C1)C2=NC(=CS2)C(=O)O)O |
| InChI | InChI=1S/C10H7NO3S/c12-8-4-2-1-3-6(8)9-11-7(5-15-9)10(13)14/h1-5,12H,(H,13,14) |
| InChI Key | UCVBEULMPJTLLH-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. The design, synthesis, and evaluation of organ-specific iron chelators
Raymond J Bergeron, Jan Wiegand, James S McManis, Neelam Bharti J Med Chem. 2006 Nov 30;49(24):7032-43. doi: 10.1021/jm0608816.
A series of iron chelators, three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid (DADFT) and three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic acid (DADMDFT) analogues are synthesized and assessed for their lipophilicity (log Papp), iron-clearing efficiency (ICE) in rodents and iron-loaded primates (Cebus apella), toxicity in rodents, and organ distribution in rodents. The results lead to a number of generalizations useful in chelator design strategies. In rodents, while log Papp is a good predictor of a chelator's ICE, chelator liver concentration is a better tool. In primates, log Papp is a good predictor of ICE, but only when comparing structurally very similar chelators. There is a profound difference in toxicity between the DADMDFT and DADFT series: DADMDFTs are less toxic. Within the DADFT family of ligands, the more lipophilic ligands are generally more toxic. Lipophilicity can have a profound effect on ligand organ distribution, and ligands can thus be targeted to organs compromised in iron overload disease, for example, the heart.
2. Pharmacokinetics of orally administered desferrithiocin analogs in cebus apella primates
R J Bergeron, W R Weimar, J Wiegand Drug Metab Dispos. 1999 Dec;27(12):1496-8.
The pharmacokinetic behavior of three iron chelators based on the desferrithiocin (DFT) pharmacophore, (S)-4, 5-dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic acid (desmethyldesferrithiocin, DMDFT, 2); (S)-4,5-dihydro-2-(2, 4-dihydroxyphenyl)-4-thiazolecarboxylic acid [4-(S)-hydroxydesazaDMDFT, 3); and (R)-2-(2-hydroxyphenyl)-4-oxazolinecarboxylic acid, the oxazoline analog of desazaDMDFT, 4, is described. Although 2 and 3 are comparably effective in inducing iron excretion upon oral administration, they exhibit markedly different plasma pharmacokinetics. Ligand 2 achieves a substantially higher plasma concentration than does 3, yet the renal clearance of these compounds is similar. The oxazoline analog 4 shows poor iron clearance when administered orally, although it remains in the plasma for extended periods. Chelator 4 demonstrates a marked capacity to bind to human serum albumin compared with the thiazoline derivatives. The possible implications for designing ligands for the treatment of transfusional iron overload are discussed.
3. Methoxylation of desazadesferrithiocin analogues: enhanced iron clearing efficiency
Raymond J Bergeron, Jan Wiegand, James S McManis, Jörg Bussenius, Richard E Smith, William R Weimar J Med Chem. 2003 Apr 10;46(8):1470-7. doi: 10.1021/jm020412d.
The impact of altering the octanol-water partition properties (log P) of analogues of desazadesferrithiocin, (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid, on the ligands' iron clearing properties is described. Increasing chelator lipophilicity can both substantially augment iron clearing efficiency in Cebus apella primates as well as alter the mode of iron excretion, favoring fecal over urinary output. The complications of iron overload are often associated with the metal's interaction with hydrogen peroxide, generating hydroxyl radicals (Fenton chemistry) and, ultimately, other related deleterious species. In fact, some iron chelators actually promote this chemistry. All of the compounds synthesized and tested in the current study are shown to be both inhibitors of the iron-mediated oxidation of ascorbate, thus removing the metal from the Fenton cycle, and effective radical scavengers.
Recommended Products
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
